Design

Chicago Advice?

We couldn’t afford a family vacation to Europe this year, so instead, we’re going to Chicago next week! We wanted to go somewhere in the United States where we could explore, eat well and also swim in a lake or ocean. And after my friend visited Chicago and showed me these snapshots of her daughter wrapped in a beach towel walking among skyscrapers, we were sold.

So, I’d love to ask: Any Chicago advice? We’d love to do it right, but we’re pretty clueless. So far, we’re planning to eat deep-dish pizza and hot dogs, and I’ve heard great things about this architectural boat tour. Thank you so much for any tips!

P.S. Past family vacations, and 10 tips for traveling with a baby.

(Jumping photo from ChicagoGuide08, via Apartment Therapy)

  1. Can anyone recommend the best time of the day to do the architectural boat tour? Is it best in the early morning or in the evenings? Thanks you!

  2. This comment has been removed by the author.

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  7. Anonymous says...

    My boyfriend just got offered a great job in Chicago. I don’t love my job here, and would obviously go with him, but I’m terrified of being so far from family (I’m from NY, we currently live in Boston). This post and the comments made me less afraid of this possibility…thank you. <3

  8. Absolutely go on the Architectural Boat Tour! I am from Chicago and enjoyed it immensely. Any of the museums in Museum Campus are great. My favorites are Adler Planetarium and Shedd Aquarium. Walk/ bike along Michigan Ave and you will get to see Millenium Park, Buckinham Fountain, Cloud Gate (aka the Bean), etc. The Chicago Art Institute is also amazing and has free entrance days. Food-wise Chicago Style Hot Dogs are always recommended (I prefer Portillos) and Deep-Dish Pizza at Bella Bacinos on Wacker Dr. (it’s small and hard to miss but by far my favorite) or Lou Malnatis. Night time: Second City Comedy Club, movies in the park (Millenium), Blue Man Group. The Loop is easy to walk around and always fun to stubmle upon new sights. Have a wonderful trip!

  9. Anonymous says...

    Go to Avec (615 W. Randolph St. 312-377-2002) for a not so intimate date night with hubby and do Downtown Dogs (804 N. Rush St. 312-951-5141) for THE BEST chicago dog ever. Must be the celery salt ;) Hope you post about those two places. Enjoy!
    -Delta :)

  10. Portillos! Both of my parents are from the Chicago area and I’m currently in school there, and we are frequent eaters at Portillos. The italian beef there is fantastic [we get it shipped to home in Florida for special occasions!] and they have plenty of other great stuff [try the cheese fries].
    I love the rest of these comments – I’m getting a few great ideas of what has to go on my to do list before I graduate and leave the city.

  11. lincoln park zoo and botanical garden is free, volare restaurant on Grand Ave. hot dougs hot dogs. On monday at 6 there is free music in millenium park and its perfect for kiddies and adults. byob and byoblanket.

  12. Free concerts at Millennium Park! So good. And you can bring wine! Wonderful. :)

  13. We just visited Chicago with a 16 month old toddler, and would highly recommend Lincoln Park (north of the river) and Millennium Park (south of the river) for when your toddler gets cranky.

    There are lots of things to see at Lincoln Park, like the Zoo and Conservatory, and we also highly recommend the Nature Museum (~$10 entry for adults) for its butterfly room. (some photos here)

    And for food, there’s RJ Grunt’s with burgers and a salad bar, and Nookies for their great breakfasts.

    Have a great time!

  14. We just visited Chicago with a 16 month old toddler, and would highly recommend Lincoln Park (north of the river) and Millennium Park (south of the river) for when your toddler gets cranky.

    There are lots of things to see at Lincoln Park, like the Zoo and Conservatory, and we also highly recommend the Nature Museum (~$10 entry for adults) for its butterfly room. (some photos here)

    And for food, there’s RJ Grunt’s with burgers and a salad bar, and Nookies for their great breakfasts.

    Have a great time!

  15. We actually just took a trip to chicago last month and loved it!

    I highly recommend having breakfast at Toast. We went 2 days in a row it was so good. We went to the one near Lincoln Park but there’s in Bucktown too. Get one of the benedicts. It’s totally kid friendly too.

    And for sure check out the Art Institute. We spent the afternoon there. They have such a diverse collection.

    I blogged about our trip here:

    http://champagnereveries.blogspot.com/2012/06/chicago-beaches.html

    http://champagnereveries.blogspot.com/2012/06/update-back-from-chicago.html

    Have a great time!

  16. You have tons of advice and I haven’t been to Chicago in almost five years, but! we were watching Diners, Drive-Ins and Dives the other day and almost hopped a plane to Chicago to try out the burger joint they spotlighted: DMK Burger Bar (http://dmkburgerbar.com/), near Wrigley Field.

    Maybe we will hop that plane…

  17. Anonymous says...

    I live in Lincoln Park– LOVE this neighborhood. Go shopping at Armitage & Halsted. Get bagels at Chicago Bagel Authority (Armitage and Sheffield). Architectural Boat Tour is great. Toby will love the LP Zoo. If you go to the LP Zoo on Saturday morning, make sure to check out the Green City Market (it’s right by the zoo) open on Saturdays from 7am-1pm. Grab lunch at RJ Grunt’s, right down the street from the zoo. ENJOY!

  18. Anonymous says...

    definitely check out the bean and millennium park. places to eat: piece pizza (not deep dsh tho) in wicker park neighborhood, lula cafe or m. henry for brunch. big star for some fun al fresco dining. piccolo sogno for italian, girl & the goat (no reservations but walk-in tables available). i love my city and hope you enjoy it too!

  19. Michelle says...

    AH! i missed this post. i was actually in Europe this week for work… but I lived in Chicago for 7 years. These are my go tos for chi-town visits

    – Catching a free show at Millenium Park ( head to goddess and grocer to pick up some snacks and vino.. as they fully allow a boozy snack on the lawn during the shows)

    – ride bikes along the lake… if you can make it up to the Field Museum.. try not to turn around and save the view from the stairs of the museum to see one of the most beautiful sights of the city…

    – tacos and micheladas at Big Star ( city’s BEST patio and BEST taco’s ) side note: Mexican food is to Chicago … what Chinese is to New York.

    – stop by Robyn Richmond and Apartment Number 9 on Damen. (right by Big Star) for some great mens and womens pieces…

    – brunch at Southport Grocer ( bread pudding pancakes = best thing EVER)

    – if you want to beach it… do Oak St. quieter and much cleaner than North Ave. beach.

    – architectural tour is a MUST

    – check out the new Modern Wing at the Art Institute Museum… im biased as I went to school there.. but it truly has one of the worlds best collections

    – Check out one of Rick Bayless’ spots for amazing mexican…

    – riding on the Brown Line.. around the loop and over the chicago river is a cheap and fun little adventure.. to see the city.. and Toby will be fascinated. It still gets me!

    – Lou Malnati’s for pizza… and no ketchup on the hotdog.. make sure it has celery salt too!.

    HAVE FUN!… Chicago is the BEST in the summer…

  20. Oh, I am SO jealous! I recently moved from Chicago (way cool) to Houston (way uncool) and miss it a ton. Hope I’m not too late to give you some ideas… Have fun and take pictures!!!

    FOOD/DRINK…
    Deep dish pizza:
    Pequod’s,
    Lou Malnati’s

    Bars:
    Northdown Cafe and Taproom (pretty low-key, great beer selection and really good food),
    Halsted’s (in Boystown, awesome tater tots and fishbowl cocktails, TVs that play music videos all day and night),
    Hopleaf Bar (a Belgian-style bar with amazing fries and mussels),
    Clark Street Ale House

    Coffee/Sweets:
    Bleeding Heart Bakery (lots of vegan items),
    Dinkel’s Bakery (amazing old-fashion donuts),
    Molly’s Cupcakes,
    Starfruit (healthy frozen kefir),
    Kickstand Espresso Bar,
    Intelligentsia Coffee and Tea

    Misc. Food, Etc.:
    Wishbone (on Lincoln Ave, awesome brunch),
    The Chicago Diner (local produce, vegan-friendly, unusual dishes),
    Duke of Perth (Scottish pub, awesome fish and chips and shepherd’s pie),
    La Creperie (French),
    Cafe Iberico (Tapas)

    COOL WANDERING SPOTS/THINGS TO SEE…
    Downtown:
    Art Institute,
    Buckingham Fountain,
    Millennium Park and “The Bean” (if you can, definitely go to a free concert in the park),
    Harold Washington Library,
    Michigan Ave from the downtown loop north to Water Tower,
    Chicago River Walk (along Wacker)

    North of Downtown:
    Old Town Neighborhood,
    Lakeview/Wrigleyville/Boystown,
    Lincoln Park Zoo (free! and pretty along the lake),
    North Ave Beach,
    Clark St. from North Ave to Diversey
    Green City Farmer’s Market (every Saturday 7am-1pm, at the south end of Lincoln Park between Clark and Stockton Drive)

    West of Downtown:
    Wicker Park Neighborhood,
    Bucktown Neighborhood

    Additional Tidbits:
    I highly recommend you get a CTA ‘weekend pass’ (or 3 day pass) I think you can get them at the CTA stations at either airport, and at some locations downtown. It’s totally worth it and super convenient!

  21. Rachel says...

    Museum of Science and Industry!

  22. And Garrets Popcorn is a MUST. Get the Chicago Mix!

  23. !See a Second City show!

  24. I will just die if the 3 of you come and eat where I work@ Nellcote or the Pump Room! Check out the Oriental Institute on the campus of the University of Chicago. The seminary co-op book store will rock your world. Plus they own a children’s book store called 57th street books. Maybe swing by the president’s house…it’s possible to do. Otherwise andersonville is full of families, shopping, food (hopleaf for the best beers, lady gregory’s for whiskey/bourbon/scotch-both best in city) + bookstore Women & children first. Have fun! Xoxo

  25. I will just die if the 3 of you come and eat where I work@ Nellcote or the Pump Room! Check out the Oriental Institute on the campus of the University of Chicago. The seminary co-op book store will rock your world. Plus they own a children’s book store called 57th street books. Maybe swing by the president’s house…it’s possible to do. Otherwise andersonville is full of families, shopping, food (hopleaf for the best beers, lady gregory’s for whiskey/bourbon/scotch-both best in city) + bookstore Women & children first. Have fun! Xoxo

  26. I will just die if the 3 of you come and eat where I work@ Nellcote or the Pump Room! Check out the Oriental Institute on the campus of the University of Chicago. The seminary co-op book store will rock your world. Plus they own a children’s book store called 57th street books. Maybe swing by the president’s house…it’s possible to do. Otherwise andersonville is full of families, shopping, food (hopleaf for the best beers, lady gregory’s for whiskey/bourbon/scotch-both best in city) + bookstore Women & children first. Have fun! Xoxo

  27. I will just die if the 3 of you come and eat where I work@ Nellcote or the Pump Room! Check out the Oriental Institute on the campus of the University of Chicago. The seminary co-op book store will rock your world. Plus they own a children’s book store called 57th street books. Maybe swing by the president’s house…it’s possible to do. Otherwise andersonville is full of families, shopping, food (hopleaf for the best beers, lady gregory’s for whiskey/bourbon/scotch-both best in city) + bookstore Women & children first. Have fun! Xoxo

  28. You must get reservations for Girl and The Goat and Mindy Seagal’s Hot chocolate; if you like beer, don’t miss the 90 beers on tap at Old Town Pour House.

    Drinks at the Signature Lounge in John Hancock Tower are a nice compromise between view and paying the ticket for Sears Tower; more than the architecture tour I would take the water taxi from Sears to Navy Pier!

  29. Jen says...

    The zoo, Nature Museum and gorgeous old Conservatory are right next to each other. You can eat at North Park restaurant on a lovely lagoon near the zoo. It has such a gorgeous view of the skyline AND there is a playground right next door! Check out North Avenue beach (less claustrophobic than Oak St). Vintage shopping in Wicker Park is fab. Architecture river boat tour (really, any architecture tour), or a sail on the lake. Galleries in River North. Also, if you want a wonderland of flowers, check out A New Leaf at the intersection of Lincoln Ave and Wells. Upstairs it is a florist housed in a magnificent old rowhouse with a carriage house in the rear, and downstairs is a hidden treat – ribbons, tiles and candles in all different shades (and no, they are not paying me to write this :).

  30. A FAVORITE of mine growing up: Indian Boundary Park. For the kiddos it has an amazing wood castle like play structure and a large water play area, a few exotic animals, a beautiful mini lake with large weeping willows. Perfect for picnicking and enjoying a quieter place in the city.
    http://www.chicagoparkdistrict.com/parks/indian-boundary-park/

  31. Anonymous says...

    Skip Navy Pier! Trust me! I’ve lived here for 10 years. NP is very touristy, very hot, crowded and nothing to do! Do visit “the bean” and the face fountains at Millennium Park. Then head out to Wicker Park for night life – best bars include Rodan, The Charleston and a bar with a fountain called The Owl.

  32. Anonymous says...

    It is funny that most posts are about food! We have some great food in Chicago. I have to say…if I was moving out of the city and could only eat one more local delicacy it would be the dounts at the Doughnut Vault. They are seriously unbelievable and one of a kind. Go early though because they sell out fast.

  33. I can’t look through all 500 comments but I have to say that you the architecture boat tour you posted is NOT the one that is best. I have lived here for only two years but have gone on about 5 architecture tours (I have had a lot of visitors). The architecture foundation is by far the best one. The people are amazingly informative and kind.

    http://www.architecture.org/tours/

  34. Heather R says...

    Since I am assuming you will be there over the 4th, try to get a hotel room that is close to the lake and towards the top of the hotel. We stayed at McCormick Place and had a room on the 30th floor. We were able to watch fireworks along the horizon in probably 30 different communities all at once. It seemed to last for hours. Also, for food I recommend Eleven City Diner (amazing challah french toast and corned beef – not at the same time, and easy to park on the street) and also Kuma’s Corner on Belmont. It can get really busy, but the metal atmostphere is entertaining and the burgers and mac and cheese are to die for. Have a blast!

  35. Anonymous says...

    The architectural boat tour is amazing! I did it last summer on my first trip to Chicago, and it made me really appreciate the city’s buildings. My guide was incredibly informative, and it allows you to see parts of the city that you wouldn’t be able to cover on foot in a weekend.

  36. Good to know for healthy, quick food downtown — Protein Bar. There are a few locations, all downtown in the loop/river north area. It’s the best for when, after all of the vacation food we all undoubtedly consume, you need a good salad, quinoa bowl or wrap. They also have breakfast and a variety of yummy protein shakes or fresh juices. http://www.theproteinbar.com/

  37. Do everything along Lakeshore Drive, go see the bean and walk along Michigan for some shopping! Go to a Second City or, if you’re feeling like a hilariously raunchy play, go see a show at the Annoyance Theater!

  38. Chicago is an awesome city! I lived there most of my life. If you get a chance though you should also head about an hour and a half north by Amtrak to Milwaukee. It’s summer and that is when the city is most alive! It’s easily a day trip as well.

    But back to Chicago. The architectural boat tour is fantastic. You can also do a kayaking architectural tour, but that might be a little difficult with the baby.

    The Field Museum and the Museum of Science and Industry are my favorites. So much to see and do in both. Also the Shedd Aquarium is fun, especially since the redesign. There is also a live show with the dolphins.

    The top of the Sears Tower is something to see, even if you don’t step out on to the see through platform. The John Hancock, also has a great view that often gets overlooked for the Sears Tower.

    Navy Pier is fun, but usually busy. There are free trolleys to Navy Pier , here is a link to the map http://www.navypier.com/visit_us/pdf/Trolley_Route_Map12.pdf

    There is also a chocolate tour of the city which is fun…and delicious.

    North avenue beach is a nice place to just relax and get some sun and enjoy the lake.

    My one restaurant recommendation is Cumin in Wicker Park. It is a mix of Indian and Nepali food. I lived in Nepal for 2 years and it is the only place that has had food that tasted like Nepal. Here is the link http://www.cumin-chicago.com/

    Okay sorry for lengthy comment, but honestly anywhere you go will be fantastic as Chicago has so much to offer!

  39. Thought of a few more places:
    Bari’s on Chicago Ave for the best Italian sub you will ever have. They get their breads from the D’Amato bakery next door and it’s amazeballs.
    Kuma’s Corner – Giant burgers on pretzel rolls. Everyone who mentioned this place is right, it’s fantastic.

  40. I’m sure you’ve already had this comment, but Wicker Park/Bucktown to eat and shop is key, but getting a bit expensive. The Musicbox Theater is killer, basically hit up the Northside to see how the folks live, I used to live in the Lincoln Square/Ravenswood area, it is the best for young families. Lots of parks. Plus if you want some cheap, but yumtastic diner food? Without any trendiness, hit up a Golden Nugget, all homemade goodness.

  41. You have to head to andersonville! M.henry is the best brunch in the city. I recommend the blackberry blisscakes or the quiche. And stop by hopleaf for a beer!

  42. Bekah says...

    Eat at Grand Luxe Cafe!!!

  43. Ooh, I live in Chicago (and have a toddler a couiple months younger than Toby) and am so excited that you will be visiting our city! I tried to post a couple of times and it doesn’t look like it worked, so sorry if this is a repeat.

    Are you here all week? I would definitely spend some time downtown and some time exploring some of the neighborhoods.

    Downtown:

    Definitely visit Millennium Park. You can check out Millenniumpark.org for events, but there are free workouts on Saturday mornings (yoga, tai chi, zumba), concerts, a family fun festival with kids’ events, The Bean (my favorite Chicago landmark), and the fountain with faces/squirting water (why can’t I remember the name of it?) that Toby can play in (bring a change of clothes–he’ll get wet).

    The aquarium is great, and one of the best views of the city skyline for photos is from out near the planetarium and aquarium.

    I know locals will say to avoid Navy Pier (touristy, crowded), but the Children’s Museum is still there (I swear it didn’t move) and is a good stop if it is too hot or rainy to be outside. I don’t know if I’d go if the weather is nice since there is so much to see and do outside.

    Definitely go to the top of the Hancock Building and have a drink in the lounge on a clear day. The view is amazing!

    If you do a boat tour I’d recommend the architecture foundation one.

    Also, I know it is touristy but I also think the red double-decker bus tours are a great way to get an overview of downtown. Plus you can get on/off at various museums.

    Lincoln Park:

    The zoo is great! There is also a farm in the zoo just south of the regular zoo that has free kids’ concerts with “Mr. Singer” on Wed. and Fri. morning (check the zoo website or call ahead to make sure). We do that a lot. I also agree with checking out the Farmer’s Market there.

    I’d recommend the Weiner Circle in Lincoln Park too. It is easier to get to than Hot Doug’s, and there won’t be a long line.

    Bucktown:

    I live in Bucktown (on the border of Wicker Park) and it is a great neighborhood to stroll, shop, and eat.

    Enjoy your trip! We’ll keep an eye out for you.

  44. The best pizza is at Lou Malnati’s! We make it a point to go there every time we visit Chicago!

  45. Anonymous says...

    Shedd or Museum of Science and Industry are both perfect for little ones. And ride the el at least once!